메뉴 건너뛰기




Volumn 59, Issue 33, 2003, Pages 6221-6231

Metal-catalysed radical cyclisations leading to N-heterocycles: New approaches to gabapentin and pulchellalactam

Author keywords

Amino acids; Cyclisations; Nitrogen heterocycles; Radical reactions

Indexed keywords

ANTICONVULSIVE AGENT; GABAPENTIN; HETEROCYCLIC COMPOUND; METAL; PULCHELLALACTAM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0042704956     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01030-5     Document Type: Article
Times cited : (62)

References (44)
  • 6
    • 0034703439 scopus 로고    scopus 로고
    • See for example: (a) Ghelfi F., Parsons A.F. J. Org. Chem. 65:2000;6249 (b) Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., Parsons A.F. Tetrahedron. 55:1999;5839 (c) Ghelfi F., Ghirardini G., Libertini E., Forti L., Pagnoni U.M. Tetrahedron Lett. 40:1999;8595 (d) Clark A.J., Battle G.M., Bridge A. Tetrahedron Lett. 42:2001;4409.
    • (2000) J. Org. Chem. , vol.65 , pp. 6249
    • Ghelfi, F.1    Parsons, A.F.2
  • 8
    • 0033521082 scopus 로고    scopus 로고
    • See for example: (a) Ghelfi F., Parsons A.F. J. Org. Chem. 65:2000;6249 (b) Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., Parsons A.F. Tetrahedron. 55:1999;5839 (c) Ghelfi F., Ghirardini G., Libertini E., Forti L., Pagnoni U.M. Tetrahedron Lett. 40:1999;8595 (d) Clark A.J., Battle G.M., Bridge A. Tetrahedron Lett. 42:2001;4409.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8595
    • Ghelfi, F.1    Ghirardini, G.2    Libertini, E.3    Forti, L.4    Pagnoni, U.M.5
  • 9
    • 0035948247 scopus 로고    scopus 로고
    • See for example: (a) Ghelfi F., Parsons A.F. J. Org. Chem. 65:2000;6249 (b) Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., Parsons A.F. Tetrahedron. 55:1999;5839 (c) Ghelfi F., Ghirardini G., Libertini E., Forti L., Pagnoni U.M. Tetrahedron Lett. 40:1999;8595 (d) Clark A.J., Battle G.M., Bridge A. Tetrahedron Lett. 42:2001;4409.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4409
    • Clark, A.J.1    Battle, G.M.2    Bridge, A.3
  • 10
    • 0036248015 scopus 로고    scopus 로고
    • For a review see: (a) Ishibashi H., Sato T., Ikeda M. Synthesis. 2002;695 (b) Chatgilialoglu C., Ferreri C., Guerra M., Timokhin V., Froudakis G., Gimisis T. J. Am. Chem. Soc. 124:2002;10765.
    • (2002) Synthesis , pp. 695
    • Ishibashi, H.1    Sato, T.2    Ikeda, M.3
  • 17
    • 0042435343 scopus 로고    scopus 로고
    • Int. Pat. Appl. WO 99/14184, 1999
    • Bryans, J. S.; Morrell, A. I. Int. Pat. Appl. WO 99/14184, 1999; Chem. Abstr., 1999, 130, 223583.
    • (1999) Chem. Abstr. , vol.130 , pp. 223583
    • Bryans, J.S.1    Morrell, A.I.2
  • 23
    • 85031140557 scopus 로고    scopus 로고
    • 3 in toluene gave 2-benzyl-4,4-dichloro-1-hydroxy-2-azaspiro[4.5]decan-3-one in only 20% yield (together with β-lactam products in 28% yield)
    • 3 in toluene gave 2-benzyl-4,4-dichloro-1-hydroxy-2-azaspiro[4.5]decan-3-one in only 20% yield (together with β-lactam products in 28% yield).
  • 27
    • 85031139415 scopus 로고    scopus 로고
    • 3SnH (added over 5 h). In addition to the simple reduced product, this gave products derived from radical fragmentation and radical fragmentation followed by 5-endo-trig cyclisation
    • 3SnH (added over 5 h). In addition to the simple reduced product, this gave products derived from radical fragmentation and radical fragmentation followed by 5-endo-trig cyclisation.
  • 29
    • 37049098678 scopus 로고
    • For related cyclisations see: (a) Nagashima H., Ara K.-I., Wakamatsu H., Itoh K. J. Chem. Soc., Chem. Commun. 1985;518 (b) Jolly R.S., Livinghouse T. J. Am. Chem. Soc. 110:1988;7536 (c) Boivin J., Yousfi M., Zard S.Z. Tetrahedron Lett. 35:1994;5629 (d) Ikeda M., Teranishi H., Nozaki K., Ishibashi H. J. Chem. Soc., Perkin Trans. 1. 1998;1691.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 518
    • Nagashima, H.1    Ara, K.-I.2    Wakamatsu, H.3    Itoh, K.4
  • 30
    • 0023757586 scopus 로고
    • For related cyclisations see: (a) Nagashima H., Ara K.-I., Wakamatsu H., Itoh K. J. Chem. Soc., Chem. Commun. 1985;518 (b) Jolly R.S., Livinghouse T. J. Am. Chem. Soc. 110:1988;7536 (c) Boivin J., Yousfi M., Zard S.Z. Tetrahedron Lett. 35:1994;5629 (d) Ikeda M., Teranishi H., Nozaki K., Ishibashi H. J. Chem. Soc., Perkin Trans. 1. 1998;1691.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7536
    • Jolly, R.S.1    Livinghouse, T.2
  • 31
    • 0027933327 scopus 로고
    • For related cyclisations see: (a) Nagashima H., Ara K.-I., Wakamatsu H., Itoh K. J. Chem. Soc., Chem. Commun. 1985;518 (b) Jolly R.S., Livinghouse T. J. Am. Chem. Soc. 110:1988;7536 (c) Boivin J., Yousfi M., Zard S.Z. Tetrahedron Lett. 35:1994;5629 (d) Ikeda M., Teranishi H., Nozaki K., Ishibashi H. J. Chem. Soc., Perkin Trans. 1. 1998;1691.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5629
    • Boivin, J.1    Yousfi, M.2    Zard, S.Z.3
  • 32
    • 33748495584 scopus 로고    scopus 로고
    • For related cyclisations see: (a) Nagashima H., Ara K.-I., Wakamatsu H., Itoh K. J. Chem. Soc., Chem. Commun. 1985;518 (b) Jolly R.S., Livinghouse T. J. Am. Chem. Soc. 110:1988;7536 (c) Boivin J., Yousfi M., Zard S.Z. Tetrahedron Lett. 35:1994;5629 (d) Ikeda M., Teranishi H., Nozaki K., Ishibashi H. J. Chem. Soc., Perkin Trans. 1. 1998;1691.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1691
    • Ikeda, M.1    Teranishi, H.2    Nozaki, K.3    Ishibashi, H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.